The structure of velutinol A is (15R,16R,20S)-14,16:15,20:16,21-triepoxy- 15,16-seco-14β,17α-pregn-5-ene-3β,15-diol. A combined quantitative Overhauser effect and molecular modelling study

Journal of the Chemical Society. Perkin Transactions 2

Volumn 7, Issue , 1996, Pages 1359-1366

  Bento, Edson S ^a,b   Calixto, João B ^c   Hawkes, Geoffrey E ^a   Pizzolatti, Moacir G ^c   Sant'Ana, Antonio E G ^b   Yunes, Rosendo A ^c  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

^b FEDERAL UNIVERSITY OF ALAGOAS   (Brazil)

^c FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000954179     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/P29960001359     Document Type: Article

References (35)

1. R. A. Yunes, M. G. Pizzolatti, A. E. G. Sant'Ana, G. E. Hawkes and J. B. Calixto, Phytochemical Analysis, 1993, 4, 76.
2. J. B. Calixto, M. Nicolau and R. A. Yunes, Br. J. Pharmacol., 1985, 85, 729.
3. J. B. Calixto, M. Nicolau, M. G. Pizzolatti and R. A. Yunes, Br. J. Pharmacol., 1987, 91, 199.
4. J. B. Calixto, M. Nicolau and R. A. Yunes, Gen. Pharmacol., 1988. 19, 595.
5. J. B. Calixto, M. G. Pizzolatti and R. A. Yunes, Br. J. Pharmacol., 1988, 94, 1133.
6. J. B. Calixto, R. A. Yunes, G. A. Rae and Y. S. Madeiros, in Bradykinin Antagonists: Basic and Clinical Research, ed. R. M. Burch, Marcel Dekker, New York, 1991, pp. 98-127.
7. J. B. Calixto, J. C. Zanini Jr., A. B. Cruz and Y. S. Madeiros, Prostaglandins, 1991, 41, 515.
8. 1H NOE occurs see D. Neuhaus and M. P. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, VCH, New York, 1989, pp. 36-38.
9. R. A. Yunes, R. L. Brum, J. B. Calixto and H. Rimpler, Phytochemistry, 1993, 34, 787.
10. J. B. Calixto and R. A. Yunes, Gen. Pharmacol., 1991, 22, 99.
11. For recent reviews of the methodology see I. L. Barsukov, L.-Y. Lian and M. J. Sutcliffe, in NMR of Macromolecules - A Practical Approach, ed. G. C. K. Roberts, Oxford University Press, Oxford, 1993, chs. 10 and 11.
12. D. Maes, M. Van Cauteren, L. Wyns, J. Lisgarten, R. Palmer, D. Lisgarten, R. Willem, M. Biesemans and F. Kayser, J. Chem. Soc., Perkin Trans. 2, 1992, 2179.
13. J. W. Blunt and J. B. Stothers, Org. Magn. Reson., 1977, 9, 439.
14. D. N. Kirk, H. C. Toms, C. Douglas, K. A. White, K. E. Smith, S. Latif and R. W. P. Hubbard, J. Chem. Soc., Perkin Trans. 2, 1990, 1567.
15. See ref. 8, p. 35.
16. J. W. Keepers and T. L. James, J. Magn. Reson., 1984, 57, 404.
17. R. Boelens, T. M. G. Koning and R. Kaptein, J. Mol. Struct., 1988, 173, 299.
18. T. M. G. Koning, R. Boelens and R. Kaptein, J. Magn. Reson., 1990, 90, 111.
19. D. T. Pegg, M. R. Bendall and D. M. Doddrell, Aust. J. Chem., 1980, 33, 1167.
20. R. Rowan, J. A. McCammon and B. D. Sykes, J. Am. Chem. Soc., 1974, 96, 4773.
21. D. E. Woessner, J. Chem. Phys., 1962, 36, 1.
22. D. E. Woessner, J. Chem. Phys., 1965, 42, 1855.
23. K. Wüthrich, M. Billeter and W. Braun, J. Mol. Biol., 1983, 169, 949.
24. K. W. Zilm, R. T. Conlin, D. M. Grant and J. Michl, J. Am. Chem. Soc., 1980, 102, 6672.
25. H. Kessler, H. Oschkinat, C. Griesinger and W. Bermel, J. Magn. Reson., 1986, 70, 106.
26. C. J. Bauer, R. Freeman, T. Frenkiel, J. Keeler and A. J. Shaka, J. Magn. Reson., 1984, 58, 442.
27. A. Bax and D. G. Davies, J. Magn. Reson., 1985, 65, 355.
28. J. K. M. Sanders and B. K. Hunter, Modern NMR Spectroscopy, Oxford University Press, Oxford, 1993, 2nd edn., chs. 4 and 5.
29. M. R. Bendall and D. T. Pegg, J. Magn. Reson., 1983, 53, 144.
30. See for example, J. A. McCammon and S. C. Harvey, Dynamics of Proteins and Nucleic Acids, Cambridge University Press, Cambridge, 1987, p. 51.
31. M. Clark, R. D. Cramer and N. Van Opdehbosch, J. Comput. Chem., 1989, 10, 982.
32. M. Blanco, J. Comput. Chem., 1991, 12, 237.
33. I. D. Kuntz, J. F. Thomason and O. S. Oshiro, Methods in Enzymol., 1989, 177, 159, and refs. therein.
34. CRC Handbook of Chemistry and Physics, ed. R. C. Weast, CRC Press, Boca Raton, 1979, 59th edn., E-56.
35. An example of this is a second component, compound 12, isolated from the rhizomes of Mandevilla velutina, which we have shown to be a pentasaccharide derivative of velutinol A: E. S. Bento, J. B. Calixto, G. E. Hawkes, A. E. G. Sant'Ana, M. G. Pizzolatti and R. A. Yunes, unpublished results.